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WO2007028661A1 - Composition de peinture en poudre hybride a faible temperature de cuisson pour des revetements semi-brillants a mats - Google Patents

Composition de peinture en poudre hybride a faible temperature de cuisson pour des revetements semi-brillants a mats Download PDF

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Publication number
WO2007028661A1
WO2007028661A1 PCT/EP2006/062873 EP2006062873W WO2007028661A1 WO 2007028661 A1 WO2007028661 A1 WO 2007028661A1 EP 2006062873 W EP2006062873 W EP 2006062873W WO 2007028661 A1 WO2007028661 A1 WO 2007028661A1
Authority
WO
WIPO (PCT)
Prior art keywords
powder coating
coating composition
composition according
carboxyl
weight
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP2006/062873
Other languages
German (de)
English (en)
Inventor
Jörn Volker Weiss
Werner Grenda
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Evonik Operations GmbH
Original Assignee
Evonik Degussa GmbH
Degussa GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Evonik Degussa GmbH, Degussa GmbH filed Critical Evonik Degussa GmbH
Priority to US12/066,325 priority Critical patent/US20080255272A1/en
Priority to EP06777262A priority patent/EP1922375A1/fr
Publication of WO2007028661A1 publication Critical patent/WO2007028661A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/03—Powdery paints
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
    • C08G59/686—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins

Definitions

  • the invention relates to low-firing hybrid powder coating compositions for semi-gloss to matt coatings, a process for their preparation and their use.
  • DE-OS 44 03 225 describes salts of pyromellitic acid and tertiary amines, which can be used for the preparation of matt epoxy and hybrid coatings.
  • the object of the present invention was to find a powder coating composition which can also be cured at temperatures well below 200 ° C, but leads to coatings with a semi-glossy to dull appearance.
  • the composition of the invention not only leads to a lowering of the baking temperature of the powder coating composition to about 160 ° C, but also at the same time produces the desired semi-glossy to matte surface of the coatings.
  • the invention relates to a powder coating composition, essentially containing
  • the carboxyl-containing polyesters A) are polyesterpolycarboxylic acids which are prepared from polyols and polycarboxylic acids or derivatives thereof.
  • the melting range of these acidic polyesters is in a range of 60 to 160 ° C, preferably 80 to 120 ° C; their acid number varies from 20 to 150 mg KOH / g, preferably 30 to 60 mg KOH / g.
  • the OH numbers should be below 10 mg KOH / g.
  • the average molecular weight (M w ) is 1000 to 5000 g / mol.
  • the polyesters are present in amounts of from 12 to 30% by weight, preferably from 15 to 25% by weight, in the powder coating composition according to the invention.
  • polyesters A) for the preparation of the polyesters A) to be used are polycarboxylic acids, such as. For example, oxalic, adipic, 2,2,4 (2,4,4) -trimethyladipine, azelaic, sebacic, decanedicarboxylic, dodecanedicarboxylic, fumaric, phthalic, isophthalic, terephthalic, trimellitic and / or pyromellitic acid used.
  • polycarboxylic acids such as.
  • polyols used by way of example: ethylene glycol, 1,2- and 1,3-propanediol, 1,2-, 1,3-, 1,4- and 2,3-butanediol, 1,5-pentanediol, 3-methyl-1, 5-pentanediol, neopentyl glycol, 1,12-dodecanediol, 2.2.4 (2.4.4) -trimethyl-1,6-hexanediol, trimethylolpropane, glycerol, pentaerythritol, 1,4-bis-hydroxymethylcyclohexane, cyclohexane-1,4-diol, diethylene glycol , Triethylene glycol and dipropylene glycol.
  • hydroxyl-containing acidic polyesters which are prepared by known processes from polycarboxylic acids and polyols, can be reacted with polycarboxylic acids and / or polycarboxylic anhydrides to the polyester polycarboxylic acids.
  • Preferred monomers are adipic, succinic, isophthalic, terephthalic, trimellitic, 1,10-decane-di- and 1,12-dodecane diacid.
  • the epoxy resins B) used are solid, resinous substances which melt in the range 60 to 150 ° C, preferably 70 to 110 ° C, and which contain on average more than one 1,2-epoxide group per molecule. In principle, all compounds which contain more than one 1,2-epoxide group per molecule are suitable. Examples are polyepoxides such as polyglycidyl ethers of aromatic or aliphatic compounds containing several hydrogen atoms. These include resorcinol, hydroquinone, pyrocatechol, bisphenol A, bisphenol F, glycerol, pentaerythritol, mannitol, sorbitol and trimethylolpropane.
  • EP resins as obtained by reacting bisphenol A or bisphenol F with epichlorohydrin.
  • EP resins based on the reaction between bisphenol A and epichlorohydrin having an EP equivalent weight of from 400 to 3,000, preferably from 800 to 1,000, in amounts of from 30 to 40% by weight.
  • the curing agent C consisting of the mono-salt of an aromatic polycarboxylic acid and a cyclic amidine, in amounts of 1.5 to 12 wt .-%, based on the sum of all starting materials used.
  • Particularly suitable is the monosalt of pyromellitic acid and phenylimidazoline, which z. B. under the product name VESTAGON B 68 by the company Degussa, Germany, is sold.
  • a customary preparation consists in adding, to an aqueous solution of pyromellitic acid at about 70 ° C., the appropriate amount of phenylimidazoline (1 mol of imidazoline per mole of acid), homogenizing the reaction mixture at 70 ° to 80 ° C. for one hour and then to room temperature is cooled. The sparingly soluble mono-salt precipitates, is filtered off, dried and then finely ground. The so produced high-melting monosalt can then be used in this form as a curing agent in the powder coating composition according to the invention.
  • tetraalkylammonium compounds, halides and carboxylates are preferably used in amounts of from 0.2 to 1.5% by weight. In particular are suitable
  • Tetraalkylammonium salts based on the following carboxylic acids: acetic, propionic, benzoic,
  • Adipic, terephthalic and isophthalic acid are particularly suitable.
  • Particularly suitable are tetraethylammonium benzoate, tetrabutylammonium benzoate, benzyltrimethylammonium chloride and
  • Tetrabutylammonium bromide Tetrabutylammonium bromide.
  • the commercially available products for example Merck, Aldrich, Fluka
  • Typical auxiliaries and additives are leveling agents, pigments and fillers, the additional amount of which can be varied in the range from 0 to 45% by weight.
  • the invention also provides a process for the preparation of a powder coating composition, essentially containing
  • At least 12 wt .-% of at least one carboxyl-containing polyester having an acid number of 20 to 150 mg KOH / g, an average molecular weight M w of 1000 to 5000 g / mol and a melting range of 60 to 160 ° C, and
  • the COOH-functionalized polyester, the epoxy resin, the curing agent, the catalyst, leveling agent, pigments and fillers are mixed together at room temperature and then homogenized on an extruder or kneader at temperatures of 100 to 140 ° C. After cooling, the extrudate is crushed, ground and then screened to a particle size ⁇ 100 microns.
  • the ratio of polyester to resin is selected to provide from 0.3 to 0.8, preferably from 0.5 to 0.6, COOH groups per epoxy group of the resin to abreaction of the residual epoxy groups of the resin Added an appropriate amount of hardener. Since the hardener also has a catalytic effect on the various reactions occurring during the firing, an exact stoichiometric calculation of the required amount of hardener for a given gloss level adjustment is not possible and must therefore be determined empirically. In order to achieve the lowest possible levels of gloss, the proportion of polyester must be low and the proportion of hardener must be relatively high.
  • the powder coating compositions according to the invention are suitable for the production of coatings having semi-glossy to preferably matt surfaces of the coatings.
  • the amounts of the individual powder coating binder components can be varied widely.
  • the application of the powder coating composition of the invention to suitable substrates can be prepared by the known methods, such. B. by electrostatic powder spraying, vortex sintering or electrostatic vortex sintering.
  • the coated substrates for curing to temperatures of 150 to 180 ° C, preferably 150 to 170 ° C, more preferably 155 to 165 ° C, 157 to 165 ° C, 158 to 162 ° C, most preferably heated at 160 ° C within 30 to 8 min.
  • the paint films produced in this way are characterized by very good flow, a good to very good mechanics and a semi-glossy to preferably matt surface, wherein the gloss level is arbitrarily adjustable over a wide range.
  • the gloss level measurement is carried out according to DESf EN ISO 2813 by means of a reflectometer whose use is described for the determination of the gloss on flat paint and coating surfaces in DIN 67 530.
  • the device can be operated at three different angles of incidence (20 °, 60 ° and 85 °), with 20 ° being used preferably for very matt and 85 ° for high-gloss surfaces; the 60 ° angle is special for gloss level measurements suitable for medium-gloss surfaces, but is also suitable for universal gloss level determination.
  • the invention also provides the use of a powder coating composition substantially containing
  • the invention further provides coatings with a semi-glossy to matt surface containing a powder coating composition, essentially containing A) at least 12 wt .-% of at least one carboxyl-containing polyester with a
  • the starting materials - hardener, epoxy resin, polyester, catalyst and leveling agent - were intimately mixed with the white pigment (TiO 2 ) in a pug mill and then homogenized in the extruder at 90 to 110 ° C. After cooling, the extrudate was crushed and ground in a pin mill to a particle size ⁇ 100 microns.
  • the powder prepared as described above was applied with an electrostatic powder spray system at 60 kV on degreased, optionally pretreated steel sheets and baked in a laboratory circulating air dryer,
  • KS you. Ball impact directly in inches * lb (ASTM D 2794-93)
  • KS rev reverse ball shot in inches * lb (ASTM D 2794-93)
  • hybrid powder coating (catalyst: tetraethylammonium benzoate, epoxy resin: polyester ratio: 67: 33)
  • VESTAGON B 68 Hardener, Degussa AG
  • EPIKOTE 1055 Epoxy Resin, CRYLCOAT 316: Polyester, Cytec
  • KRONOS 2220 titanium dioxide, Kronos
  • TEAB tetraethylammonium benzoate, Fluka
  • hybrid powder coating (based on tctrabutylammonium bromide
  • VESTAGON B 68 Hardener, Degussa AG
  • KRONOS 2220 titanium dioxide, Kronos
  • VESTAGON B 68 Hardener, Degussa AG
  • EPIKOTE 1055 Epoxy Resin, Resolution KRONOS 2220: Titanium Dioxide, Kronos
  • TEAB tetraethylammonium benzoate
  • Fluka Coatings Testing

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Paints Or Removers (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)

Abstract

L'invention concerne une composition de peinture en poudre hybride à faible température de cuisson pour des revêtements semi-brillants à mats.
PCT/EP2006/062873 2005-09-09 2006-06-02 Composition de peinture en poudre hybride a faible temperature de cuisson pour des revetements semi-brillants a mats Ceased WO2007028661A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US12/066,325 US20080255272A1 (en) 2005-09-09 2006-06-02 Hybrid-Powder Paint Composition Having a Low Burning Temperature For Semi-Glossy to Matt Coverings
EP06777262A EP1922375A1 (fr) 2005-09-09 2006-06-02 Composition de peinture en poudre hybride a faible temperature de cuisson pour des revetements semi-brillants a mats

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102005042822.3 2005-09-09
DE102005042822A DE102005042822A1 (de) 2005-09-09 2005-09-09 Hybrid-Pulverlackzusammensetzung mit niedriger Einbrenntemperatur für halbglänzende bis matte Überzüge

Publications (1)

Publication Number Publication Date
WO2007028661A1 true WO2007028661A1 (fr) 2007-03-15

Family

ID=36754276

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2006/062873 Ceased WO2007028661A1 (fr) 2005-09-09 2006-06-02 Composition de peinture en poudre hybride a faible temperature de cuisson pour des revetements semi-brillants a mats

Country Status (5)

Country Link
US (1) US20080255272A1 (fr)
EP (1) EP1922375A1 (fr)
CN (1) CN1927969B (fr)
DE (1) DE102005042822A1 (fr)
WO (1) WO2007028661A1 (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110224459A1 (en) 2010-03-11 2011-09-15 Evonik Degussa Gmbh Beta-hydroxyalkylamides, a method for production of same and use of same
US8476376B2 (en) 2010-03-11 2013-07-02 Evonik Degussa Gmbh Heat-curing powder-lacquer compositions yielding a matte surface after curing of the coating, as well as a simple method for production of same
CN103160182B (zh) * 2013-02-22 2016-05-18 安徽华辉塑业科技股份有限公司 无光型环氧粉末涂料及其制备方法
CN106536592B (zh) * 2014-07-25 2020-12-01 帝斯曼知识产权资产管理有限公司 无光泽粉末涂层
CN108034045A (zh) * 2018-01-16 2018-05-15 浙江光华科技股份有限公司 一种高填补遮痕粉末涂料用聚酯树脂及其制备方法
CN112048057A (zh) * 2020-09-11 2020-12-08 安徽鑫友高分子新材料科技有限公司 环氧树脂、应用及高流平的超低温固化型纯粉末涂料

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5488932A (en) * 1977-12-05 1979-07-14 Toyobo Co Ltd Resin composition for coating powder
EP0194904A1 (fr) * 1985-02-08 1986-09-17 Norsolor S.A. Procédé de préparation des compositions de revêtement en poudre à base d'une résine époxy et d'un polyester carboxyle
US5244944A (en) * 1991-06-05 1993-09-14 Eastman Kodak Company Thermosetting powder coating compositions
JP2001106965A (ja) * 1999-10-06 2001-04-17 Shikoku Chem Corp ビスイミダゾリン化合物のカルボン酸塩を用いたエポキシ／ポリエステル系粉体塗料
JP2002235032A (ja) * 2001-02-13 2002-08-23 Shikoku Chem Corp エポキシ／ポリエステル系粉体塗料
EP1475399A1 (fr) * 2003-05-03 2004-11-10 Degussa AG Compositions solides pour revêtements en poudre de polyuréthane à groupements uretdione et durcissables à basses températures
DE10348965A1 (de) * 2003-10-22 2005-05-25 Degussa Ag Epoxidgruppenhaltige Pulverlackzusammensetzungen, die bei niedrigen Temperaturen aushärten

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AT333917B (de) * 1973-05-16 1976-12-27 Veba Chemie Ag Verfahren zur herstellung von matten uberzugen
GB9112051D0 (en) * 1991-06-05 1991-07-24 Shell Int Research Epoxy resin powder coating composition
US7223477B2 (en) * 2000-12-05 2007-05-29 Alpha Coating Technologies, Llc Coating powders having enhanced flexability
US20110224459A1 (en) * 2010-03-11 2011-09-15 Evonik Degussa Gmbh Beta-hydroxyalkylamides, a method for production of same and use of same

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5488932A (en) * 1977-12-05 1979-07-14 Toyobo Co Ltd Resin composition for coating powder
EP0194904A1 (fr) * 1985-02-08 1986-09-17 Norsolor S.A. Procédé de préparation des compositions de revêtement en poudre à base d'une résine époxy et d'un polyester carboxyle
US5244944A (en) * 1991-06-05 1993-09-14 Eastman Kodak Company Thermosetting powder coating compositions
JP2001106965A (ja) * 1999-10-06 2001-04-17 Shikoku Chem Corp ビスイミダゾリン化合物のカルボン酸塩を用いたエポキシ／ポリエステル系粉体塗料
JP2002235032A (ja) * 2001-02-13 2002-08-23 Shikoku Chem Corp エポキシ／ポリエステル系粉体塗料
EP1475399A1 (fr) * 2003-05-03 2004-11-10 Degussa AG Compositions solides pour revêtements en poudre de polyuréthane à groupements uretdione et durcissables à basses températures
DE10348965A1 (de) * 2003-10-22 2005-05-25 Degussa Ag Epoxidgruppenhaltige Pulverlackzusammensetzungen, die bei niedrigen Temperaturen aushärten

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 003, no. 109 (C - 058) 12 September 1979 (1979-09-12) *
PATENT ABSTRACTS OF JAPAN vol. 2000, no. 21 3 August 2001 (2001-08-03) *
PATENT ABSTRACTS OF JAPAN vol. 2002, no. 12 12 December 2002 (2002-12-12) *
TSUYOSHI TOYOTA: "Imidazole and imidazoline derivatives for Powder coating application", 2000, PROCEEDINGS OF THE ANNUAL MEETING TECHNICAL PROGRAM OF THE FEDERATION OF SOCIETIES FOR COATINGS TECHNOLOGY, XX, XX, XP008067720 *

Also Published As

Publication number Publication date
CN1927969B (zh) 2011-03-02
DE102005042822A1 (de) 2007-03-22
CN1927969A (zh) 2007-03-14
EP1922375A1 (fr) 2008-05-21
US20080255272A1 (en) 2008-10-16

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